EP1448069B1 - Mittel zum schutz gegen verderb - Google Patents

Mittel zum schutz gegen verderb Download PDF

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Publication number
EP1448069B1
EP1448069B1 EP02803120A EP02803120A EP1448069B1 EP 1448069 B1 EP1448069 B1 EP 1448069B1 EP 02803120 A EP02803120 A EP 02803120A EP 02803120 A EP02803120 A EP 02803120A EP 1448069 B1 EP1448069 B1 EP 1448069B1
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EP
European Patent Office
Prior art keywords
preventive agent
sterol
deterioration preventive
oil
deterioration
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
EP02803120A
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English (en)
French (fr)
Other versions
EP1448069A1 (de
Inventor
Tadahiro c/o Takasago Int. Corp. Hiramoto
Haruo c/o Takasago Int. Corp. ARAI
Toshinori c/o Takasago Int. Corp. SAIMA
Masashi c/o Takasago Int. Corp. OTSUKA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Takasago International Corp
Original Assignee
Takasago International Corp
Takasago Perfumery Industry Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2001349799A external-priority patent/JP4038787B2/ja
Priority claimed from JP2001349800A external-priority patent/JP2003144114A/ja
Application filed by Takasago International Corp, Takasago Perfumery Industry Co filed Critical Takasago International Corp
Publication of EP1448069A1 publication Critical patent/EP1448069A1/de
Application granted granted Critical
Publication of EP1448069B1 publication Critical patent/EP1448069B1/de
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/06—Treating tea before extraction; Preparations produced thereby
    • A23F3/14—Tea preparations, e.g. using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • A23F3/163—Liquid or semi-liquid tea extract preparations, e.g. gels, liquid extracts in solid capsules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/70—Comminuted, e.g. emulsified, fish products; Processed products therefrom such as pastes, reformed or compressed products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/349—Organic compounds containing oxygen with singly-bound oxygen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/2024—Monohydric alcohols cyclic; polycyclic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to a deterioration preventive agent, which is useful for preventing deterioration of foods and fragrance-containing products. More specifically, the present invention relates to a food-deterioration preventive agent and a deterioration preventive agent for fragrance-containing products, which contains a sterol as the active ingredient.
  • WO-A-0179400 discloses the use of phytosterols as antioxidants for deterioration prevention in food and cosmetics.
  • the phytosterols (plant source) disclosed have the same skeleton structure as formula 1.
  • US-A-4234577 discloses antioxidant compositions comprising sterols with the same skeleton structure as formula 1, and their addition to food products to protect against oxidation.
  • EP-A-0875232 discloses adding, to perfume-containing cosmetics, a sterol composition with the same skeleton structure as formula 1.
  • JP-A-62148424 discloses adding a sterol-containing composition to food products or chemicals, to prevent deterioration.
  • JP-A-56042546 discloses a combined use of a phytosterol and a sucrose fatty acid ester to prevent the feathering phenomenon of a coffee whitener.
  • WO-A-9918811 discloses the use of flavonoids as warmed-over flavor inhibiting substances.
  • GB-A-884688 discloses a composition for conditioning the skin and retarding the rate of moisture loss, comprising inter alia some sterols.
  • EP-A-0897671 discloses an aqueous phase dispersion or suspension comprising high melting lipids, e.g. phytosterols, and a non-sterol emulsifier.
  • perfumes For the purpose of satisfying consumer's preference, it is common to add perfumes to various products such as oral care products and toiletry products.
  • the fragrance-containing products are influenced by light, heat, air and so forth during each stage of the manufacturing process, distribution process and storage, and various problems, e.g., change of quality of aroma and disappearance of the aroma in some cases, result in.
  • various problems e.g., change of quality of aroma and disappearance of the aroma in some cases, result in.
  • fragrance-containing products themselves are made alkaline, many fragrance components have a defect that they are susceptive to alkaline condition, so that problems, e.g., loss of quality of aroma over the course of time, are pointed out.
  • these stabilizers are unable to stabilize fragrance-containing products to a satisfactory degree.
  • the stabilizers stabilize the products to only a small degree.
  • a sterol having a skeleton represented by the following formula 1 as a deterioration preventive agent for perfume-containing products in alkaline conditions.
  • the sterol is obtained from:
  • the sterol has 27 to 30 carbon atoms.
  • the sterol is sito sterol, stigma-sterol, campe-sterol, spinasterol or brassica-sterol, or glycerides thereof.
  • the above perfume-containing product may be a food.
  • the above-mentioned food is a drink, a frozen confection, a dessert, a fermented milk food, a dairy product, a confection or a fish paste.
  • the above-mentioned perfume-containing product may be a cosmetic, a toiletry product, a domestic cleaning product, a detergent for lavatories, a detergent for bathrooms, a powder detergent for washing, a detergent for automatic dishwasher, a fabric softener or a deodorant.
  • the cosmetic is a perfume.
  • the deterioration preventive agent of the invention contains a sterol as the active ingredient.
  • the deterioration preventive agent is excellent in an effect to prevent the deterioration of perfumes such as flavor and fragrance.
  • the deterioration preventive agent is useful as a food-deterioration preventive agent or a deterioration preventive agent for fragrance-containing products.
  • the sterol is excellent in an effect to prevent the deterioration of dough in foods or flavors of foods or flavors that are to be newly added and blended to foods.
  • the foods blended with the food-deterioration preventive agent containing the sterol as the active ingredient can realize long-term quality retention.
  • the dough herein means an unscented food, i.e., the food before a flavor is added thereto.
  • the sterol is excellent in an effect to prevent the deterioration of fragrance to be added and blended to fragrance-containing products.
  • the fragrance-containing products blended with the deterioration preventive agent for fragrance-containing products containing the sterol as the active ingredient can realize long-term quality retention.
  • said fragrance-containing products mean products to which fragrances are added and blended for improving consumer's satisfaction, such as so-called detergents, bleaching agents and toiletry products, for example, below-mentioned products as specific examples.
  • the sterols used in the invention include all the compounds having a skeleton represented by the following formula 1.
  • the sterols include, for example, the compound represented by the formula 1, derivatives of the compound represented by the formula 1, glycosides thereof, or mixtures thereof.
  • the derivatives include compounds wherein hydrogen atom(s) of each of the compounds represented by the formula 1 are substituted by organic group(s) such as alkyl group(s).
  • the sterols used in the invention may be widely present in plants, animal tissues, and microorganisms.
  • Representative plants containing sterol(s) include vegetables such as Japanese radish leaves, lettuce, asparagus, cucumber, egg bonnet, oriental pickling melon, garlic, horsetail and Japanese ginger, grains or plant seeds such as unpolished rice, rice bran, buckwheat, sesame seeds, sunflower seeds, walnuts, peanuts and rapeseeds, soybean or soybean-derived products such as bean-curd refuse, rice oil, sesame oil, rape oil, cottonseed oil, olive oil, soybean oil, palm oil, coconut oil, and the like.
  • vegetables such as Japanese radish leaves, lettuce, asparagus, cucumber, egg bonnet, oriental pickling melon, garlic, horsetail and Japanese ginger, grains or plant seeds such as unpolished rice, rice bran, buckwheat, sesame seeds, sunflower seeds, walnuts, peanuts and rapeseeds, soybean or soybean-derived products such as bean-curd refuse, rice oil, sesame oil, rape oil, cottonseed oil, olive oil, soybean oil, palm oil,
  • Microorganisms containing sterol(s) include yeast and the like.
  • Animal tissues containing sterol(s) include fish oils, animal oils such as whale, tallow, and the like.
  • stigma-sterol As the sterols present in plants, stigma-sterol, sito sterol, campe-sterol, spina-sterol, brassica sterol, and the like can be referred to.
  • ergosterols As the sterols present in microorganisms, ergosterols and the like can be referred to.
  • sterols present in animals cholesterol and the like can be referred to.
  • sterols derived from plants and microorganisms in view of food deterioration preventive ability, fragrance-containing products deterioration preventive ability and easiness of preparation.
  • phytosterols are preferred, and specific examples of the preferred sterols include phytosterols such as sito sterol, stigma-sterol, campesterol, spina-sterol and brassica-sterol, or glycerides thereof.
  • the sterols used in the invention may be commercially available products or may be prepared by a conventional method such as molecular distillation or extraction using animal tissues, plants and microorganisms containing the above sterols as starting materials. Also, the above sterols are main components of unsaponifiable matter of animal and vegetable oils and fats, and hence the sterols may be prepared from them by said conventional method.
  • the materials are generally subjected to pre-treatment.
  • the pre-treatment includes, for example, a method wherein starting materials are dried and then finely crushed. Subsequently, the thus treated starting materials are brought into contact with a solvent to transfer the sterols to the solvent layer.
  • the solvent include hydrocarbons such as toluene, hexane, benzene and petroleum ether, halogenated hydrocarbons such as chloroform, esters such as ethyl acetate, and alcohols such as ethanol and methanol.
  • solvents may be used alone or as mixtures of two or more of them, such as a mixed solvent of chloroform/methanol.
  • a mixed solvent of chloroform/methanol and alcohols such as ethanol, and particularly preferred is ethanol.
  • sterols may be prepared by a usual method.
  • JP-B-40-17599 discloses a deodorizing treatment of a crude vegetable oil obtained by solvent extraction. When the method is carried out, that is, steam is blown into the above crude vegetable oil under high temperature and high pressure, scum is produced and sterols can be precipitated and separated from the scum using hexane, methanol or the like.
  • sterols When sterols are prepared using unsaponified matter of animal and vegetable oils and fats, as starting materials, it is usually subjected to pre-treatment such as saponification to remove reaction products, and then sterols are transferred to a solvent layer by contact with solvent.
  • the operations thereafter are basically the same as the operations in the case of solvent extraction using a plant containing the above sterols as the starting material.
  • the operations wherein sterols are prepared using for example wool wax (lanolin) or the like as a starting material are basically the same as the operations in the case of solvent extraction using a plant containing the above sterols as the starting material.
  • solvent containing sterol(s) may be used as a deterioration preventive agent such as a food-deterioration preventive agent or a deterioration preventive agent for fragrance-containing products, as it is.
  • a deterioration preventive agent such as a food-deterioration preventive agent or a deterioration preventive agent for fragrance-containing products of the invention is prepared by heating and evaporating the solvent to obtain a concentrate and then applying a usual purification method.
  • the purification method include, for example, a silica gel column chromatography.
  • a silica gel column chromatography there may be adopted a method wherein the above concentrate is poured into a column packed with silica gel beforehand to load the concentrate on the silica gel and then eluent composed of solvent(s) is poured into the column to elute retained matter together with the solvent(s), and the eluting solvent(s) are separated into several fractions by a known means.
  • solvent(s) there may be used hydrocarbons such as n-pentane, n-hexane, branched hexanes, benzene and toluene, ethers such as ethyl ether, esters such as ethyl acetate and methyl acetate, alcohols such as methanol, ethanol, n-propanol and 2-propanol, and the like.
  • hydrocarbons such as n-pentane, n-hexane, branched hexanes, benzene and toluene
  • ethers such as ethyl ether
  • esters such as ethyl acetate and methyl acetate
  • alcohols such as methanol, ethanol, n-propanol and 2-propanol, and the like.
  • solvents may be used alone or as mixtures of two or more of them.
  • silica gel column chromatography elution with hex
  • the mixing ratio of each of the solvents is not particularly limited.
  • the elution is usually carried out at room temperature but the temperature is not particularly limited, and the elution may be also carried out under a low temperature or under a high temperature.
  • deterioration preventive agent of the invention containing a sterol is useful as a food-deterioration preventive agent or a deterioration preventive agent for fragrance-containing products.
  • the food-deterioration preventive agent of the invention can realize the retention of the quality of foods by adding and blending the food-deterioration preventive agent into foods.
  • Examples of foods whose deterioration can be prevented by adding and blending into the foods include drinks such as non-fruit juice drinks, fruit juice drinks, lactobacillus drinks, powder drinks, tea drinks and coffee drinks, frozen confections such as ice cream, sherbet and ice confections, desserts such as pudding, jelly and Bavarian cream, fermented milk foods such as hard yogurt, soft yogurt, yogurt drinks and frozen yogurt, dairy products such as butter, margarine and cheese, confections such as gum, pies and candy, fish pastes, and the like.
  • the amount of food-deterioration preventive agent blended in the foods varies depending on the kind of foods, it is normally added in an amount of 0.1 ppm to 1% by weight, preferably added in an amount of 1 ppm to 0.1% by weight, in the products.
  • a method may be used in which it is added and blended directly into the above objective foods or a method may be used in which a solution or dispersion of the food-deterioration preventive agent is preliminarily prepared and then this solution or dispersion is added and blended into the foods.
  • the latter method is preferred.
  • Various additives such as thickeners and antioxidants may be present beforehand in this solution or dispersion.
  • Examples of medium used to obtain the above solution or dispersion include alcohols such as ethanol, medium chain fatty acid esters of glycerin or the like, purified vegetable oils such as coconut oil and corn salad oil, and edible oils.
  • the amount of the food-deterioration preventive agent to be added to the medium varies considerably depending on the food to which the agent is added and blended, and so forth, the amount is, for example, from 10 ppm to 50% by weight.
  • examples of representative fragrances whose deterioration can be prevented by the deterioration preventive agent for fragrance-containing products include citrus-base, fruit-base and mint-base fragrances. Also, fragrances each containing an aliphatic aldehyde as the main fragrant component may be mentioned.
  • the deterioration preventive agent for fragrance-containing products of the invention exhibits an effect that the quality of fragrance-containing products can be retained by adding and blending the deterioration preventive agent for fragrance-containing products into fragrance-containing products.
  • fragrance-containing products whose deterioration can be prevented by adding and blending, into the fragrance-containing products, the deterioration preventive agent for fragrance-containing products of the invention include cosmetics such as fragrance, skin care, make-up, hair cosmetics, toiletry products such as shampoos, hair treatments, body shampoos, solid soaps, bath agents, toothpastes, tooth liquid, and mouthwashes, domestic cleaning products, detergents for lavatories, detergents for bathrooms, powder detergents for washing, detergents for automatic dishwasher, fabric softeners and deodorants.
  • cosmetics such as fragrance, skin care, make-up, hair cosmetics, toiletry products such as shampoos, hair treatments, body shampoos, solid soaps, bath agents, toothpastes, tooth liquid, and mouthwashes, domestic cleaning products, detergents for lavatories, detergents for bathrooms, powder detergents for washing, detergents for automatic dishwasher, fabric softeners and deodorants.
  • the amount of deterioration preventive agent for fragrance-containing products blended in the fragrance-containing products varies depending on the kind of fragrance-containing products, it is normally added in an amount of 0.01 ppm to 1% by weight, preferably added in an amount of 0.1 ppm to 1% by weight, and more preferably added in an amount of 1 ppm to 0.1% by weight, in the products.
  • a method may be used in which it is added and blended directly into the above objective fragrance-containing products or a method may be used in which a solution or dispersion of the deterioration preventive agent for fragrance-containing products is preliminarily prepared and then this solution or dispersion is added and blended into the fragrance-containing products.
  • the latter method is preferred.
  • Various additives such as thickeners and antioxidants may be present beforehand in this solution or dispersion.
  • Examples of medium used to obtain the above solution or dispersion include alcohols such as ethanol, medium chain fatty acid esters of dipropylene glycol, glycerin or the like, purified vegetable oils such as coconut oil and corn salad oil, and edible oils.
  • the amount of the deterioration preventive agent for fragrance-containing products to be added to the medium varies considerably depending on the fragrance-containing product to which the agent is added and blended, and so forth, the amount is, for example, from 10 ppm to 50% by weight%.
  • the sample was sterilized by packing it in a transparent PET container, followed by immersion at 80°C for 10 minutes. Also, for heat-aging test, the sample was sterilized by packing it in a can container, followed by retort sterilization at 121°C for 10 minutes.
  • Samples for evaluation were prepared in the same manner as in Example 3 with the exception that the deterioration preventive agent (b) of Example 2 (0.001, 0.01 or 0.1% by weight) was added instead of the deterioration preventive agent (a) of Example 1.
  • Example 3 Samples were prepared in the same manner as in Example 3 with the exception that 10% ethanol solution of chlorogenic acid was added in an amount of 0.1% instead of the deterioration preventive agent (a). These samples were subjected to sensory evaluation under the same conditions as in Example 3. The results are shown in Tables 1 and 2. Table 1. Light-aging test results Added concentration (ppm) Sensory evaluation 6 days Comparative Example 1 Control - D (D) Comparative Example 2 Chlorogenic acid 100 D (D) Example 3 Deterioration preventive agent (a) 10 B (B) 100 A (A) Example 4 Deterioration preventive agent (b) 0.1 B (B) 1 A (A) 10 A (A)
  • the "added concentration” means the added concentration in terms of solid matter. Moreover, the character in parenthesis shows evaluation with regard to taste and another shows evaluation with regard to aroma (these shall apply similarly hereinafter).
  • Table 2 Heat-aging test results Added concentration (ppm) 1 week 2 weeks Comparative Example 1 Control - D (D) D (D) Comparative Example 2 Chlorogenic acid 100 D (D) D (D) Example 3 Deterioration preventive agent (a) 10 B (B) B (B) 100 A (A) A (A) Example 4 Deterioration preventive agent (b) 0.1 B (B) B (C) 1 A (A) B (B) 10 A (A) A (A)
  • the “added concentration” means the added concentration in terms of solid matter.
  • Bean-curd refuse was dried at 50°C over a period of one day and night.
  • the deterioration preventive agent (c) having a final concentration of 10% was prepared from the dried product in the same manner as in Example 1.
  • the samples were sterilized by packing it in a transparent PET container, followed by immersion at 80°C for 10 minutes. Also, for heat aging test, the samples were sterilized by packing it in a can container, followed by retort sterilization at 121°C for 10 minutes.
  • Samples for evaluation were prepared in the same manner as in Example 6 with the exception that the deterioration preventive agent (b) of Example 2 was added in an amount of 0.001, 0.01 or 0.1% by weight instead of the deterioration preventive agent (c) of Example 5.
  • Example 6 Samples were prepared in the same manner as in Example 6 with the exception that 10% ethanol solution of chlorogenic acid was added in an amount of 0.1% instead of the deterioration preventive agent (c). These samples were subjected to sensory evaluation in the same manner as in Example 6. The results are shown in Tables 3 and 4. Table 3. Light-aging test results Added concentration (ppm) Sensory evaluation 6 days Comparative Example 3 Control - D (D) Comparative Example 4 Chlorogenic acid 100 D (D) Example 6 Deterioration preventive agent (c) 10 B (B) 100 A (A) Deterioration preventive agent (b) 0.1 B (B) Example 7 1 A (A) 10 A (A)
  • the "added concentration” means the added concentration in terms of solid matter.
  • Table 4 Heat-aging test results Added concentration (ppm) Sensory evaluation 1 week 2 weeks Comparative Example 3 Control - D (D) D (D) Comparative Example 4 Chlorogenic acid 100 D (D) D (D) Example 6 Deterioration preventive agent (c) 10 B (B) B (B) 100 A (A) B (B) Example 7 Deterioration preventive agent (b) 0.1 B (B) B (B) 1 A (A) B (B) 10 A (A) B (B)
  • the “added concentration” means the added concentration in terms of solid matter.
  • the gum base, powder sugar and starch syrup described in the following formulation were thoroughly kneaded in a kneader. Citric acid was added thereto and the whole was continued to knead. Furthermore, a flavor and a deterioration preventive agent (b) were added thereto and the mixture was continued to knead for thorough mixing (50°C, 30 minutes). The kneaded product was extruded to obtain a chewing gum having width, length and thickness of 20 mm, 70 mm and 2 mm, respectively.
  • Chewing gum formulation Gum base 21% Starch syrup 13% Lemon flavor 1% Citric acid 1.4% Deterioration preventive agent (b) 0.1% Powder sugar 63.5% Total 100.0%
  • the above sample was subjected to aging test under the following conditions.
  • the chewing gum of Example 8 to which the deterioration preventive agent (b) is added is definitely superior to the chewing gum of Comparative Example 5 to which no deterioration preventive agent is added and also to the chewing gum of Comparative Example 6 to which vitamin E is added instead of the deterioration preventive agent (b).
  • Tooth paste base formulation Heavy calcium carbonate 50.00 Glycerin 25.00 Purified water 21.80 Carboxymethyl cellulose 1.50 Sodium lauryl sulfate 1.40 Saccharin sodium 0.25 Monosodium benzoate 0.05 Total 100.00
  • Example 9 Sample was prepared in the same manner as in Example 9 with the exception that ethanol was added in an amount of 0.1% instead of the deterioration preventive agent (b). The sample was subjected to evaluation under the same condition as in Example 9. The results are shown in Table 5.
  • Example 9 Sample was prepared in the same manner as in Example 9 with the exception that 1% ethanol solution of vitamin E mix was added in an amount of 0.1% instead of the deterioration preventive agent (b). The sample was subjected to evaluation under the same condition as in Example 9. The results are shown in Table 5. Table 5 Added concentration (ppm) Evaluation Comment Comparative Example 7 Control - D Aroma totally deteriorates remarkably, and particularly fruity smell decreases drastically. Comparative Example 8 Vitamin E mix 10 D As in non-addition plot, aroma totally deteriorates remarkably.
  • Example 9 Deterioration preventive agent (b) 0.1 B Fruity smell and sweetness remain but sweetness derived from mint slightly deteriorates. 1 A Totally, aroma most resembles that of unaged one, and deterioration is hardly observed.
  • the “added concentration” means the added concentration in terms of solid matter.
  • the deterioration preventive agent (b) can significantly improve stability of flavor over the course of time in an added concentration of 0.1 ppm and 1 ppm without affecting smell and appearance of toothpastes.
  • the agent is effective for preventing deterioration of perfumes in alkaline bases, the deterioration being hitherto a problem.
  • a mouthwash base having the following formulation were added 0.1% by weight of a mouthwash flavor (mint-base type) and 0.01% by weight of the deterioration preventive agent (b) of Example 2, whereby a mouthwash was obtained.
  • This mouthwash was packed into two 100 ml transparent glass bottles, and the bottles were tightly closed.
  • Mouthwash base formulation 95% ethyl alcohol 10.00 Polyoxyethylene-hardened castor oil (EO-60) 2.00 Conc.
  • Example 10 Sample was prepared in the same manner as in Example 10 with the exception that ethanol was added in an amount of 0.01% instead of the deterioration preventive agent (b). The sample was subjected to evaluation under the same condition as in Example 10. The results are shown in Table 6.
  • Example 10 Sample was prepared in the same manner as in Example 10 with the exception that 1% ethanol solution of vitamin E mix was added in an amount of 0.01% instead of the deterioration preventive agent (b). The sample was subjected to evaluation under the same condition as in Example 10. The results are shown in Table 6. Table 6 Added concentration (ppm) Evaluation Comment Comparative Example 9 Control - D Aroma totally deteriorates remarkably, and particularly fruity smell decreases drastically. Comparative Example 10 Vitamin E mix 1 D As in non-addition plot, aroma totally deteriorates remarkably.
  • the “added concentration” means the added concentration in terms of solid matter.
  • the deterioration preventive agent (b) can significantly improve stability of flavor over the course of time in an added concentration of 1 ppm without affecting smell and appearance of mouthwash.
  • Example 11 Application to a detergent for automatic dish washer
  • Fragrance-deterioration preventive ability of the deterioration preventive agent (b) of Example 2 was evaluated with the following samples.
  • a fragrance-containing detergent for automatic dishwasher having the following formulation was prepared. (% by weight) Formulation: Water 27.14 Bentonite (Polargel T) 1.00 Monostearyl phosphate 0.16 Sodium hydroxide (solid matter 49%) 4.00 Sodium carbonate 4.50 Sodium silicate RU 14.00 Sodium hypochlorite (5.25%) 23.00 Calcium tripolyphosphate (Ca-TPP) 24.00 Sodium decylphenyl ether sulfate (Dowfax 3B-2) 1.20 Citrus-base fragrance 1.00 Total 100.00
  • the above citrus-base fragrance was obtained by adding the deterioration preventive agent (b) in an amount of 1% to a citrus-base fragrance.
  • fragrance-containing detergent for automatic dishwasher were stored at 40°C for 2 months, and then, evaluated in accordance with the following evaluation standard.
  • the characteristic of the deterioration preventive agent of the invention is to contain a sterol as the active ingredient.
  • a sterol as the active ingredient.
  • the invention is economically advantageous since it is enough to blend a small amount of the deterioration preventive agent.
  • the deterioration preventive agent of the invention containing the sterol into fragrance-containing products, retention of quality of fragrance-containing products for a long period of time is enabled.
  • the invention is economically advantageous since it is enough to blend a small amount of the deterioration preventive agent for fragrance-containing products.
  • the deterioration preventive agent for fragrance-containing products of the invention is excellent in an effect to prevent the deterioration of non-fragrance containing products.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Botany (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Mycology (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Zoology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Confectionery (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • General Preparation And Processing Of Foods (AREA)

Claims (8)

  1. Verwendung eines Sterols mit einem Gerüst, das durch die folgende Formel 1 wiedergegeben wird:
    Figure imgb0005
     als ein Mittel zur Verhinderung des Verderbs bzw. der Zersetzung für Duftstoff enthaltende Produkte in alkalischen Milieus.
  2. Verwendung nach Anspruch 1, wobei das Sterol erhalten wird aus:
    - einer Gemüsepflanze ausgewählt aus der Gruppe bestehend aus Blättern des Japanischen Rettichs, Salat bzw. Lattich, Spargel, Gurke, Froschblatt (brasenia schreberi), Gemüsemelone, Knoblauch, Schachtelhalm und Japanischem Ingwer, Körnerfrüchten oder Pflanzensamen wie unpoliertem Reis, Reiskleie, Buchweizen, Sesamsamen, Sonnenblumensamen, Walnüssen, Erdnüssen und Rapssamen, Sojabohnen oder von Sojabohnen abgeleiteten Produkten wie Sojakuchen, Reisöl, Sesamöl, Rapsöl, Baumwollsamenöl, Olivenöl, Sojabohnenöl, Palmöl, Kokosnussöl;
    - einer Hefe;
    - einem tierischen Öl ausgewählt aus der Gruppe bestehend aus Walöl und Talg; oder
    - einem Fischöl.
  3. Verwendung nach Anspruch 1 oder 2, wobei das Sterol 27 bis 30 Kohlenstoffatome aufweist.
  4. Verwendung nach einem der Ansprüche 1 bis 3, wobei es sich bei dem Sterol um Sitosterol, Stigmasterol, Campesterol, Spinasterol oder Brassicasterol oder Glyceride davon handelt.
  5. Verwendung nach einem der Ansprüche 1 bis 4, wobei das Duftstoff enthaltende Produkt ein Nahrungsmittel ist.
  6. Verwendung nach Anspruch 5, wobei das Nahrungsmittel ein Getränk, ein gefrorenes Konfekt, ein Dessert, eine fermentierte Milchspeise, ein Molkereiprodukt, ein Konfekt oder eine Fischpaste ist.
  7. Verwendung nach einem der Ansprüche 1 bis 4, wobei das Duftstoff enthaltende Produkt ein Kosmetikum, ein Toilettenartikel, ein Hausreinigungsprodukt, ein Detergens für Waschräume bzw. Toiletten, ein Detergens für Badezimmer, ein pulverförmiges Detergens zum Waschen, ein Detergens für eine Geschirrspülmaschine, ein Textilweichspüler oder ein Deodorant ist.
  8. Verwendung nach Anspruch 7, wobei das Kosmetikum ein Duftstoff bzw. ein Parfüm ist.
EP02803120A 2001-11-15 2002-11-14 Mittel zum schutz gegen verderb Expired - Fee Related EP1448069B1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2001349799 2001-11-15
JP2001349800 2001-11-15
JP2001349799A JP4038787B2 (ja) 2001-11-15 2001-11-15 香料の劣化防止剤
JP2001349800A JP2003144114A (ja) 2001-11-15 2001-11-15 食品劣化防止剤および食品の品質保持方法
PCT/JP2002/011895 WO2003041517A1 (en) 2001-11-15 2002-11-14 Deterioration preventive agent

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EP1448069B1 true EP1448069B1 (de) 2009-06-03

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US20050175745A1 (en) * 2004-02-06 2005-08-11 Jerzy Zawistowski Method of preservation of a food prodcut and composition comprising one or more phytosterols and/or phytostanols useful for this purpose
DE202009007704U1 (de) * 2009-06-02 2009-08-20 Hurtig, Sven Zahnreinigungsmittel

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GB884688A (en) * 1959-03-25 1961-12-13 Warner Lambert Pharmaceutical Skin conditioning composition
US4234577A (en) * 1979-03-19 1980-11-18 Z-L Limited Partnership Ergostadientriols, compositions containing same, and methods of preparing and using same
JPS5642546A (en) * 1979-09-13 1981-04-20 Nisshin Oil Mills Ltd:The Coffee whitener
JPS593181B2 (ja) * 1981-01-07 1984-01-23 三栄化学工業株式会社 糖類の褐変化防止法
JPH0659164B2 (ja) * 1985-12-23 1994-08-10 理研ビタミン株式会社 ステリン含有組成物
JP2922984B2 (ja) * 1990-06-01 1999-07-26 株式会社ロッテ チューインガム用香味組成物
FI105887B (fi) * 1996-09-27 2000-10-31 Suomen Sokeri Oy Elintarvike- ja terapeuttisiin sovelluksiin käyttökelpoiset, kasvisterolia sisältävät tuotteet, menetelmä niiden valmistamiseksi ja niiden käyttö
EP0875232B1 (de) * 1997-05-02 2002-02-13 Takasago International Corporation Flüssigkristallphase enthaltende Lipidzusammensetzung
US6423363B1 (en) * 1997-08-22 2002-07-23 Lipton, Division Of Conopco, Inc. Aqueous dispersion
FI973929A (fi) * 1997-10-10 1999-04-11 Itara H K Ab Oy WOF inhibiittori
JP3636073B2 (ja) * 1999-03-31 2005-04-06 日本油脂株式会社 多糖類−ステロール誘導体含有化粧料
ES2235979T3 (es) * 1999-11-03 2005-07-16 Forbes Medi-Tech Inc. Composiciones que comprenden aceites o grasas comestibles asi como fitosteroles y/o fitostanoles disueltos.
AU2001255286A1 (en) * 2000-04-14 2001-10-30 Mars, Incorporated Extraction of sterols from cocoa hulls
JP2002317192A (ja) * 2001-04-20 2002-10-31 Takasago Internatl Corp 香料組成物

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US20040265444A1 (en) 2004-12-30
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EP1448069A1 (de) 2004-08-25
BR0214158A (pt) 2004-09-28
DE60232539D1 (de) 2009-07-16

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